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Single‐Molecule Observation of Intermediates in Bioorthogonal 2‐Cyanobenzothiazole Chemistry
- Source :
- Angewandte Chemie (International Ed. in English)
- Publication Year :
- 2020
- Publisher :
- Wiley, 2020.
-
Abstract
- We report a single‐molecule mechanistic investigation into 2‐cyanobenzothiazole (CBT) chemistry within a protein nanoreactor. When simple thiols reacted reversibly with CBT, the thioimidate monoadduct was approximately 80‐fold longer‐lived than the tetrahedral bisadduct, with important implications for the design of molecular walkers. Irreversible condensation between CBT derivatives and N‐terminal cysteine residues has been established as a biocompatible reaction for site‐selective biomolecular labeling and imaging. During the reaction between CBT and aminothiols, we resolved two transient intermediates, the thioimidate and the cyclic precursor of the thiazoline product, and determined the rate constants associated with the stepwise condensation, thereby providing critical information for a variety of applications, including the covalent inhibition of protein targets and dynamic combinatorial chemistry.<br />Better off alone: A nanoreactor approach was used to investigate the chemistry of2‐cyanobenzothiazole (CBT), an important bioorthogonal reagent, at the single‐molecule level. Reactions with thiols and aminothiols revealed mechanistic and kinetic information with important implications for several essential applications of CBT reagents.
- Subjects :
- tetrahedral intermediates
Nanoreactor
single-molecule studies
010402 general chemistry
01 natural sciences
Catalysis
chemistry.chemical_compound
Reaction rate constant
Dynamic combinatorial chemistry
Molecule
nanoreactors
Research Articles
010405 organic chemistry
Thiazoline
General Medicine
General Chemistry
bioorthogonal chemistry
Combinatorial chemistry
0104 chemical sciences
chemistry
Covalent bond
click chemistry
Click chemistry
Single‐Molecule Studies | Very Important Paper
Bioorthogonal chemistry
Research Article
Subjects
Details
- ISSN :
- 15213773 and 14337851
- Volume :
- 59
- Database :
- OpenAIRE
- Journal :
- Angewandte Chemie International Edition
- Accession number :
- edsair.doi.dedup.....5735135b38339e1ebf80d62b4c651566